8-Aminovaleric acid

Archer, owing to very unfortunate coincidences, had mistaken acid potassium tartrate for the acetylamino acid. Goldfarb et al. prepared authentic 5-acetylamino-2-thiophenecarboxylic acid, mp 230 232°C (methyl ester, mp 171-171.5°C ethyl ester, mp 161°C), through reduction of 5-nitro-2-thiophenecarboxylic acid with Raney nickel in acetic anhydride and proved the structure by Raney nickel desulfurization to 8-aminovaleric acid. They also confirmed that the acid mp 272-273°C (methyl ester, mp 135-136°C ethyl ester, mp 116-117°C) is 4-acetylamino-2-thiophenecar boxy lie acid as originally stated by Steinkopf and Miiller. The statement of Tirouflet and Chane that the acid obtained upon reduction and acetylation of 5-nitro-2-thiophenecarboxylic acid melts at 272°C must result from some mistake as they give the correct melting point for the methyl ester. 

CH3.(CH2)2.C(C02.C2H5XC0.N3) mw 198.23 N 21.20% OB to C02 -153.36% ypl oil, expl. Sol in eth and CC14. Prepn is by reacting the K salt, of the half (or mono) ethyl ester of propyl malonic acid with nitrous acid Refs 1) Beil, not found 2) T. Curtius W, Lehmann, Transformation of alkylated malonic acids into a-amino acids. III. Synthesis of cr-aminovaleric acid, propylmalonylazidic acid. . JPraktChem 125, 211-302 (1930) CA 24, 3215(1930)... 

Revelles O, M Espinosa-Urgel, S Molin, JL Ramos (2004) The davDT operon of Pseudomonas putida, involved in lysine catabolism, is induced in response to the pathway intermediate 5-aminovaleric acid. J Bacterial 186 3439-3446. 

Amino-o-toluenesulfonic acid, a206 2-Amino-1,1,3-tricyanopropene, a267 1 -Aminotricyclo[3.3.l3 7]decane, a65 Aminouracil, al53 2-Aminovaleric acid, a248 5-Aminovaleric acid, a249 AMP, a216... 

Molecular imprinting is not limited to organic polymer matrices, but can also be applied to silica-based materials and even proteins. Proteins freeze-dried in the presence of a transition state analogue as template have been used successfully as catalysts, e.g., for the dehydrofluorination of a fluorobutanone. For instance, lyophilized 3-lactoglobulin imprinted in this manner with N-isopropyl-N-ni-trobenzyl-amine could accelerate the dehydrofluorination by a factor of 3.27 compared to the non-imprinted protein see Table 5 [62]. In a similar procedure, BSA was imprinted with N-methyl-N-(4-nitrobenzyl)-S-aminovaleric acid and showed an enhancement of the catalytic effect by a factor of 3.3 compared to the control protein for the same reaction see Table 5 [113]. 

Baneqee A, Das AK, Drew MGN, Baneqee A. Supramolecular parallel 8-sheet and amyloidlike fibril forming peptides using S-aminovaleric acid residue. Tetrahedron 2005 61 5906-5914. 

In principle every compound with an amino and a carboxy group can be used for such purpose ranging from simple co-amino acids [e.g., 5-aminopentanoic acid (6-aminovaleric acid) (1, n = 3)]1541 or 6-aminohexanoic acid (e-aminocaproic acid) (1, n = 4)]135,57,4 791 and related derivatives of 3-aminobenzoic acid 14801 or more sophisticated structures. A few examples (1-6) are shown in Scheme 28. Numerous cyclic turn mimetics have been developed in the past years and for details on this subject the reader is directed to Vol. E 22c, Section 12. To explore the rigidification introduced by nonnatural amino acids or equivalent structures into cyclic peptides, a careful NMR conformational analysis is required, since frequently the so-called p-turn mimetics do not enable such turns to be established, conversely other secondary structure elements may be induced.14811... 

The dimethylene replacement 4 is used to investigate the influence of rigidity. The use of 5-aminovaleric acid as a Glytj)[CH2—CH2] GIy replacement has been extended to other coamino acids as a means to influence the distance between crucial amino acid residues, and to function as a flexible spacer, replacing parts of the peptide. 

Aminovaleric acid, AE87 2-Amino-m-xylene, AN79... 

Aminouracil, a 155 2-Aminovaleric acid, a253 5-Amino valeric acid, a254 Amyl compounds, see Pentyl Amyl alcohol, p37 act-Amyl alcohol, ml53 sec-Amyl alcohol, p38 tert-Amyl alcohol, ml54 tert-Amylamine, d601... 

Fmoc-amino acids used as building blocks of testing compounds are as follows Fmoc-Asp(OtBu)-OH, Fmoc-Cys(Trt)-OH, Fmoc-Asn(Trt)-OH, Fmoc-Gln(Trt)-OH, Fmoc-Met-OH, Fmoc-Glu(OtBu)-OH, Fmoc-Lys (Boc)-OH, Fmoc-Ile-OH, Fmoc-His(Trt)-OH, Fmoc-Tyr(tBu)-OH, Fmoc-Arg(Pmc)-OH, Fmoc-Phe-OH, Fmoc-Ser(tBu)-OH, Fmoc-Thr(tBu)-OH, Fmoc-Val-OH, Fmoc-Pro-OH, Fmoc-Trp(Boc)-OH, Fmoc-D-Ala-OH, Fmoc-D-Arg(Pmc)-OH, Fmoc-D-Trp(Boc)-OH, Fmoc-D-Cys(Trt)-OH, Fmoc-D-Asp(OtBu)-OH, Fmoc-D-Glu(OtBu)-OH, Fmoc-D-His(Trt)-OH, Fmoc-D-Gln(Trt)-OH, Fmoc-D-Leu-OH, Fmoc-D-Met-OH, Fmoc-D-Pro-OH, Fmoc-D-Ser(tBu)-OH, Fmoc-D-Lys(Boc)-OH, Fmoc-D-Tyr(tBu)-OH, Fmoc-D-Thr(tBu)-OH, Fmoc-D-Phe-OH, Fmoc-D-Asn(Trt)-OH, Fmoc-3-(4-pyridyl)alanine, Fmoc-D-3-(3-pyridyl)alanine, Fmoc-4-tert-butoxyproline, Fmoc-3-chlorophenylalanine, Fmoc-norleucine, Fmoc-2-cyclohexylglycine, Fmoc-2-aminoisobutyric acid, Fmoc-tranexamic acid, Fmoc-(i ,S)-3-amino-3-(2-furyl)propionic acid, Fmoc-(i ,S)-(6,7-di-methoxy)-l,2,3,4-tetrahydroquinoline-3-carboxylic acid, Fmoc- (R, S)-3-amino-3-(4-hydroxyphenyl)propionic acid, Fmoc-(i ,S)-3-aminovaleric acid, Fmoc-(i ,5 )-3-amino-3-(3,4-dichlorophenyl)propionic acid, Fmoc-isonipecotic acid, Fmoc-(i ,S)-3-amino-3-(3,4-methylenedioxyphenyl)... 

Salts of a-oxo-S-aminovaleric acid and a-oxo-e-aminocapric acid92 93 exist as such in the solid state, but in solution they are in equilibrium with the cyclic compounds, J 1-pyrroline-2-carboxylic acid and J1Tpiperideine-2-carboxylic acid, respectively.94... 

Another hydroxylated product of OH modification of proline is 5-hydroxy-2-aminovaleric acid, arising from oxidation of proline and arginine residues (A20) (Fig. 4). 

Fig. 4. Oxidation of arginine. 5-Hydroxy-2-aminovaleric acid, which is the arginine oxidation end product, may also be produced during oxidation of proline.

The o-phthaldialdehyde derivatives of glutamate, y-aminobutyric acid (GABA), and S-aminovaleric acid (DAVA internal standard) were separated on an Altex Ultrasphere ODS column (4.6 mm x 250 mm, 5 /tin). The mobile phase contained 0.2 M sodium acetate (pH 3.8), 100 mg/mL EDTA, and 40% acetonitrile (v/v). Detection was by fluorescence, with excitation and detection wavelengths of 330 and 440 nm, respectively. 

Glutamic acid decarboxylase was assayed in a final volume of 100 / L containing 40 /tL of 200 mAf potassium phosphate buffer (pH 6.8), 10 / L of 5 mM L-glutamic acid, 5 / L of 0.2 mAf pyridoxal 5 -phosphate, 40 /tL of homogenate (2 mg protein/mL), and 1 fig of gabaquline (inhibitor of y-aminobutyric acid degradation). The reaction was stopped by the addition of 10 fiL of 100% trichloroacetic acid. After centrifugation, 5 fiL of standard 8-aminovaleric acid solution and 90 fiL of o-phthaldehyde solution (2 mg/mL 0.4 M borate buffer, pH 10.4) was added and the mixture was allowed to react for 3 to 5 minutes before injection of 20 fiL into the HPLC system. The reaction was linear for 20 minutes. 

Oximes of cyclojjentanone and cyclohexanone undergo the Beckmann rearrangement to cyclic amides from which amino acids may be obtained, e.g., S-aminovaleric acid (71-80%) and e-aminocaproic acid (92%). ... 

Some relationships between the dipole moment and molecular structure have also been found in the case of aliphatic compounds. In the first instance we may mention the two methyl esters of a- and 8-aminovaleric acid. We should expect from the results for the aminobenzoic acids that in an open chain the moment of the 8-ester would be greater than that of the a-ester, while in a chain joined into a ring the moments should be about the same. The values obtained... 

In addition to the acid chlorides listed in Table 1, Fmoc-protected anoino acid chlorides of 6-aminovaleric acid l and Tyr(tBu)l l were prepared and used in peptide synthesis, but these derivatives were contanninated with impurities due to their low stability. 

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